Acetic Acid → Eicosa-5,8,11,14-tetraenoic acid (4-chloro-benzyl)-(2,4-dichloro-phenyl)amide

HRID 392605

反応式

HRID 392605 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[Cl:10][C:11]1[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:12]=1[NH2:13].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[C:37](O)(=[O:57])[CH2:38][CH2:39][CH2:40]/[CH:41]=[CH:42]\[CH2:43]/[CH:44]=[CH:45]\[CH2:46]/[CH:47]=[CH:48]\[CH2:49]/[CH:50]=[CH:51]\[CH2:52][CH2:53][CH2:54][CH2:55][CH3:56].C(Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C.ClCCCl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:13]([C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[Cl:10])[C:37](=[O:57])[CH2:38][CH2:39][CH2:40][CH:41]=[CH:42][CH2:43][CH:44]=[CH:45][CH2:46][CH:47]=[CH:48][CH2:49][CH:50]=[CH:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])=[CH:4][CH:3]=1

参加物

10

反応物 6

HCID 176Acetic AcidHCID 77264-ChlorobenzaldehydeHCID 111232,4-DichloroanilineHCID 65578Oxalyl chlorideHCID 444899Arachidonic AcidHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 73022406Eicosa-5,8,11,14-tetraenoic acid (4-chloro-benzyl)-(2,4-dichloro-phenyl)amide収率 91%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

Used the same procedure as above to synthesize 1.15 g (56%) of the desired amine from 4-chlorobenzaldehyde (1.0 g, 7.11 mmol), 2,4-dichloroaniline (1.27 g, 7.83 mmol), sodium triacetoxyborohydride (2.41 g, 11.38 mmol), acetic acid (0.41 mL, 7.11 mmol) and 1,2-dichloroethane (32 mL). 1H NMR δ4.36 (d, 2H, 5.8 Hz), 4.73 (br.s, 1H), 6.46 (d, 1H, 8.5 Hz), 7.03 (dd, 1H, 8.7, 2.2 Hz), 7.22-7.34 (m, 5H). Used the same procedure as above for generating the acid chloride and the subsequent condensation product: used arachidonic acid (234 mg, 0.77 mmol) in CH2Cl2 (5 mL) with oxalyl chloride (147 μL, 1.69 mmol) and DMF (2 drops). The acid chloride in CH2Cl2 (3 mL) was subsequently added to the respective amine (1.1 g, 3.84 mmol) in CH2Cl2 (5 mL). Isolated the desired product (O-2248; 400 mg, 91%) after purification by column chromatography (hexanes/EtOAc 97%/3% then 95%/5%) as a single rotomer. 1H NMR δ0.88 (t, 3H, 6.9 Hz), 1.24-1.41 (m, 6H), 1.67 (q, 2H, 7.1 Hz), 1.94 -2.05 (m, 6H), 2.75 (m, 6H), 4.03 (d, 1H, 14.3 Hz), 5.22-5.40 (m, 8H), 5.48 (d, 1H, 14.3 Hz), 6.70 (d, 1H, 8.5 Hz), 7.10-7.28 (m, 5H), 7.52 (d, 1H, 2.2 Hz). Anal. Calcd for C33H40NOCl3: C, 69.33; H, 7.06. Found: C, 69.17; H, 7.20.

出典と根拠

ORDレコード
ord-1d24f0ebcd6746e7a155adb22639a804
出典データセット
uspto-grants-2004_10
特許番号
US06800770B2

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